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Levonorgestrel is a hormonal medication which is used in a number of birth control methods.
Common side effects include nausea, breast tenderness, headaches, and increased, decreased, or irregular menstrual bleeding.
Levonorgestrel was discovered in 1963 and was introduced for medical use together with ethinylestradiol in 1970.
Contents
1 Medical uses
1.1 Birth control
1.2 Emergency birth control
1.3 Hormone therapy
1.4 Available forms
2 Contraindications
3 Side effects
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 Androgenic activity
6.1.2 Antigonadotropic effects
6.2 Pharmacokinetics
7 Chemistry
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
9.4 Accessibility
10 Research
11 References
12 External links
Medical uses
Birth control
See also: Ethinylestradiol/levonorgestrel
At low doses, levonorgestrel is used in monophasic and triphasic formulations of combined oral contraceptive pills, with available monophasic doses ranging from 100–250 µg, and triphasic doses of 50 µg/75 µg/125 µg.
At very low daily dose of 30 µg, levonorgestrel is used in some progestogen-only pill
formulations.
Levonorgestrel is the active ingredient in a number of intrauterine devices including Mirena and Skyla.
Emergency birth control
Levonorgestrel is used in emergency contraceptive pills (ECPs), both in a combined Yuzpe regimen which includes estrogen, and as a levonorgestrel-only method. The levonorgestrel-only method uses levonorgestrel 1.5 mg (as a single dose or as two 0.75 mg doses 12 hours apart) taken within 3 days of unprotected sex, with one study indicating that beginning as late as 120 hours (5 days) after intercourse could be effective.
The primary mechanism of action of levonorgestrel as a progestogen-only emergency contraceptive pill is, according to International Federation of Gynecology and Obstetrics (FIGO), to prevent fertilization by inhibition of ovulation and thickening of cervical mucus.
Other studies still find the evidence to be unclear.
In November 2013, the EMA also approved a change to the label for HRA Pharma’s NorLevo saying: “In clinical trials, contraceptive efficacy was reduced in women weighing 75 kg
Hormone therapy
Levonorgestrel is used in combination with an estrogen in menopausal hormone therapy.
Available forms
Levonorgestrel is available alone in emergency contraceptive pills and progestogen-only pills, in combination with ethinylestradiol in birth control pills, in combination with estradiol valerate in oral tablets for use in menopausal hormone therapy, in combination with estradiol in a transdermal patch for use in menopausal hormone therapy, alone as an intrauterine device for use in hormonal birth control, and alone as a subcutaneous birth control implant.
Contraindications
Known or suspected pregnancy is a contraindication of levonorgestrel as an emergency contraceptive.
Side effects
See also: Progestin § Side effects
After intake of 1.5 mg levonorgestrel in clinical trials, very common side effects (reported by 10% or more) included: hives, dizziness, headache, nausea, abdominal pain, uterine pain, delayed menstruation, heavy menstruation, uterine bleeding, and fatigue ; common side effects (reported by 1% to 10%) included diarrhea, vomiting, and painful menstruation ; these side effects usually disappeared within 48 hours.
Overdose
Overdose of levonorgestrel as an emergency contraceptive has not been described.
Interactions
If taken together with drugs that induce the CYP3A4 cytochrome P450 liver enzyme, levonorgestrel may be metabolized faster and may have lower effectiveness.
Pharmacology
Pharmacodynamics
Levonorgestrel is a progestogen ; that is, an agonist of the progesterone receptor (PR), the main biological target of the progestogen sex hormone progesterone.
Relative affinities (%) of levonorgestrel and metabolites
Compound
PR
AR
ER
GR
MR
SHBG
CBG
Levonorgestrel
150–162
34 a, 45
0
1–8
17–75
50
0
5α-Dihydrolevonorgestrel
50
38 a
0
?
?
?
?
3α,5α-Tetrahydrolevonorgestrel
?
?
0.4
?
?
?
?
3β,5α-Tetrahydrolevonorgestrel
?
?
2.4
?
?
?
?
Values are percentages (%). Reference ligands (100%) were promegestone for the PR, metribolone ( a = mibolerone ) for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG. Sources:
Androgenic activity
Levonorgestrel is a weakly androgenic progestin and in women may cause androgenic side effects such as decreased sex hormone-binding globulin (SHBG) levels, decreased HDL cholesterol levels, weight gain, and acne.
Antigonadotropic effects
In men, levonorgestrel causes marked suppression of circulating testosterone levels secondary to its antigonadotropic effects.
Pharmacokinetics
The bioavailability of levonorgestrel is approximately 95% (range 85 to 100%).
Chemistry
See also: List of progestogens, List of androgens/anabolic steroids, and Norgestrel
Levonorgestrel, also known as 17α-ethynyl-18-methyl-19-nortestosterone or as 17α-ethynyl-18-methylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone.
History
Norgestrel ( rac -13-ethyl-17α-ethynyl-19-nortestosterone), the racemic mixture containing levonorgestrel and dextronorgestrel, was discovered by Hughes and colleagues at Wyeth in 1963 via structural modification of norethisterone (17α-ethynyl-19-nortestosterone).
Levonorgestrel, taken alone in a single high dose, was first evaluated as a form of emergency contraception in 1973.
Levonorgestrel has also been introduced for use as a progestogen-only intrauterine device under the brand names Mirena and Skyla among others, as a progestogen-only birth control implant under the brand names Norplant and Jadelle, as a combined oral tablet with estradiol valerate for menopausal hormone therapy under the brand name Klimonorm, and as a combined transdermal patch with estradiol for menopausal hormone therapy under the brand name Climara Pro.
Society and culture
Generic names
Levonorgestrel is the generic name of the drug and its INN, USAN, USP, BAN, DCIT, and JAN, while lévonorgestrel is its DCF.
Brand names
Levonorgestrel is marketed alone or in combination with an estrogen (specifically ethinylestradiol, estradiol, or estradiol valerate ) under a multitude of brand names throughout the world, including Alesse, Altavera, Alysena, Amethia, Amethyst, Ashlyna, Aviane, Camrese, Chateal, Climara Pro, Daysee, Emerres, Enpresse, Erlibelle, Escapelle, Falmina, Introvale, Isteranda, Jadelle, Jaydess, Jolessa, Klimonorm, Kurvelo, Kyleena, Lessina, Levlen, Levodonna, Levonelle, Levonest, Levosert, Levora, Liletta, Loette, Logynon, LoSeasonique, Lutera, Lybrel, Marlissa, Microgynon, Microlut, Min-Ovral, Miranova, Mirena, My Way, Myzilra, Next Choice, Nordette, Norgeston, NorLevo, Norplant, Option 2, Orsythia, Ovima, Ovranette, Plan B, Plan B One-Step, Portia, Postinor, Postinor-2, Preventeza, Ramonna, Rigevidon, Quartette, Quasense, Seasonale, Seasonique, Skyla, Sronyx, Tri-Levlen, Trinordiol, Triphasil, Triquilar, Tri-Regol, Trivora, and Upostelle, among many others. These formulations are used as emergency contraceptives, normal contraceptives, or in menopausal hormone therapy for the treatment of menopausal symptoms.
As an emergency contraceptive, levonorgestrel is often referred to colloquially as the “morning-after pill”.
Availability
See also: List of progestogens available in the United States
Levonorgestrel is very widely marketed throughout the world and is available in almost every country.
Accessibility
Levonorgestrel-containing emergency contraception is available over-the-counter in some countries, such as the United States.
A policy update in 2015 required all Indian Health Services -run pharmacies, clinics, and emergency departments to have Plan B One-Step in stock, to distribute it to any woman (or her representative) who asked for it without a prescription, age verification, registration or any other requirement, to provide orientation training to all staff regarding the medication, to provide unbiased and medically accurate information about emergency contraception, and to make someone available at all times to distribute the pill in case the primary staffer objected to providing it on religious or moral grounds.
Research
Levonorgestrel has been studied in combination with androgens such as testosterone and dihydrotestosterone as a hormonal contraceptive for men.

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